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Hydrolysis of Esters and Amides by the Metallo Nucleophile Tp Cum,Me Zn–OH
Author(s) -
Ruf Michael,
Vahrenkamp Heinrich
Publication year - 1996
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19961290908
Subject(s) - chemistry , nucleophile , hydrolysis , zinc , hydroxide , tris , stoichiometry , medicinal chemistry , cleavage (geology) , stereochemistry , organic chemistry , catalysis , biochemistry , geotechnical engineering , fracture (geology) , engineering
The molecular zinc hydroxide complex Tp Cum,Me ZnOH [ 1 , Tp Cum,Me = tris(3‐cumenyl‐5‐methylpyrazolyl)hydroborate] is a powerful nucleophile. It effects stoichiometric hydrolysis of activated esters RCOOX and amides RCONHX in nonaqueous media. The cleavage products are Tp Cum,Me ZnOCOR and HOX or H 2 NX, resp. Two of them (Tp Cum,Me ZnOCOCH 2 ‐CH 2 OH resulting from propiolactone and Tp Cum,Me ZnOCOCF 3 resulting from trifluoroacetamide) were characterized by crystal structure determinations.